2-Bromo-3'-chloro-4'-fluoroacetophenone → (R)-1-(2-(3-chloro-4-fluorophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 453693Notes

Reaction equation

HRID 453693 reaction equation
[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=1)=[O:29]>CCOC(C)=O>[Br-:26].[Cl:37][C:32]1[CH:31]=[C:30]([C:28](=[O:29])[CH2:27][N+:13]23[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]2)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]3)[CH:35]=[CH:34][C:33]=1[F:36]

Participants

4

Reactant 2

HCID 27827852-Bromo-3'-chloro-4'-fluoroacetophenoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660303(R)-1-(2-(3-chloro-4-fluorophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in EtOAc (5 ml), was added 2-bromo-1-(3-chloro-4-fluorophenyl)ethanone (61.7 mg, 0.24 mmol), and the reaction was stirred at room temperature for 15 hours. The precipitate was collected by suction filtration to obtain (R)-1-(2-(3-chloro-4-fluorophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (120.3 mg, 92% yield).

Workup

  1. filtrationThe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-d6852931e90c4cdb87567321710e36da
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

Loading…